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Four new azaphilones, sclerotiorins A&#8722;D (<b>1</b>&#8722;<b>4</b>), as well as the dimeric sclerotiorin E (<b>5</b>) of which we first determined its absolute configuration, and 12 known analogues (<b>5</b>&#8722;<b>16</b>) were isolated from the fermentation broth of <i>Penicillium sclerotiorum</i> OUCMDZ-3839 associated with a marine sponge <i>Paratetilla</i> sp.. The new structures, including absolute configurations, were elucidated by spectroscopic analyses, optical rotation, ECD spectra, X-ray single-crystal diffraction, and chemical transformations. Compounds <b>11</b> and <b>14</b> displayed significant inhibitory activity against &#945;-glycosidase, with IC₅₀ values of 17.3 and 166.1 &#956;M, respectively. In addition, compounds <b>5</b>, <b>7</b>, <b>10</b>, <b>12</b>&#8722;<b>14,</b> and <b>16</b> showed moderate bioactivity against H1N1 virus.